


So Not Life At All

by JamesValley



Category: Original Work
Genre: Gay, M/M, Masturbation, Mutual Pining, NSFW, Trans Female Character, Trans Male Character, Transgender, huge crush may also have a huge crush on him, poor gay trans guy has a huge crush
Language: English
Status: In-Progress
Published: 2016-05-23
Updated: 2016-05-23
Packaged: 2018-06-10 05:29:57
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,003
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6941797
Author URL: https://archiveofourown.org/users/JamesValley/pseuds/JamesValley
Summary: <blockquote class="userstuff">
              <p>Life's hard when you're a horny teenage boy and you're transgender.</p>
<p>Chester Hanes has spent his whole life being the anxious and awkward boy he is. His huge crush on the flirty boy from his literature class doesn't help. He just wants one summer to be great before he heads off to college.</p>
<p>warning: explicit and gay</p>
<p>(The song "Bitch of Living" really works well with this, sorry I've been listening to Spring Awakening a lot lately)</p>
            </blockquote>





	1. Just Give It Time, Kid

**Author's Note:**

> hi, i haven't written in forever and none of this has been proofread and im doing a ton of this really early in the morning, but hey, a boy's gotta do something right? also there will def be a ton more lgbt+ characters, mainly trans ones and a lot of this is gonna be pretty explicit at times, anyways hope u like, give me some notes on what u like/what u dont, this is just for fun none of this is really serious im just bored and theres not like a ton of media like this at all so im just filling the gap u know
> 
> alright peace my pals enjoy

"Fuck," a breath of air comes from his lips as he comes down from his high. Chester runs his free hand through his hair, making the still damp strands stick up. He sighs heavily, sitting up slowly and pulls his hand from between his thighs.

Life's hard for a teenage boy. A horny teenage boy. A horny teenage boy who couldn't get alone for just a few hours.

Life's even harder when you have to try and imagine what everything feels like. Chester was a virgin on all levels. A sex virgin, a kiss virgin, a hug virgin, even a fucking hand holding virgin. At least he was creative.

After running his hand through his hair again, he pops his other hand's fingers into his mouth, quickly and satisfyingly sucking them clean. It wasn't his best session, he wasn't much out of breath and definitely wasn't as sweaty as he could be unfortunately. Still, he opens the window, lights a candle, and turns on the fan. Chester, being the anxious boy he was, really didn't want to risk any one of his family smelling anything close to sex in his room.

He shoves a large sweatshirt over his torso, covering his bare chest and then some, the sweater reaching close to his knees. He pulls his boxers up as well, clean, despite a small wet patch on the inside.

With his heart still beating faster than normal he makes his way to the bathroom shared with his siblings. One, a nerdy little teen, tall despite being nearly four years younger than his older brother. The other an alternative 16 year old bi girl who's run through several girlfriends and whose current obsession is a boy she runs off with to the bike park every day. To be honest though, despite loving his little sister dearly, she kind of embarrassed Chester. Beating him to all the bases and, well, Chester's definitely walked in on her and her new flame more than once.

He locks the door behind him, leaving himself in a yellow ish bubble of privacy. Turning to the mirror above the sink he stares at himself, face still flushed pink below his freckles and his hair standing in all directions.

"This is such a waste," he thinks, pulling the sweatshirt off to stare at his body. "Such a waste that I'm the only person who gets to see this."

Then his face immediately flushes red as he thinks of someone he'd want to see this. Hands dropping his sweater and now covering his face, his pulse going much faster than it ever has, he groans.

Life's hard when you're a horny teenage boy with the biggest crush on another teenage boy.

Chester turns on the sink and begins to splash cool water over his face, trying to get rid of the blush and heart flutters that came with think about Daniel Halls.

The two had meet earlier in the school year, sitting near each other in a literature class run by a very, very old man. For the first few weeks there was a seating chart, one leaving Chester at his own table, a podium blocking the view from the teacher's desk, and then Daniel at the table on the other side of the podium, sitting with a good friend.

Chester really didn't have many thoughts about the other boy, sure he was tall and scruffy with nice blue eyes, definitely his type, but he couldn't tell much else.

Then, when Daniel's friend was absent one day, Daniel sat in the empty seat next to Chester. Chester, of course, assumed it was to get closer to the pretty girl who sat at the table next to Chester's.

Then, even on days when Lilly wasn't there (she was so pretty and nice though, Chester was super pleased to be acquainted with such a pretty girl) and when Daniel's friend was, Daniel would sit right next to Chester.

The two got along pretty well, even on days when the teachers voice droned on, making even Shakespeare super boring.

And then, Daniel began to do something even Chester couldn't believe. Daniel began to flirt.

On days when the teacher wasn't at his podium, instead leaving the class to listen to an audio of some poor bored soul reading Beowulf, Daniel would reach across the table, a farther reach than Chester would expect since Daniel was left-handed, and doodle small stars on Chester's work sheets. Chester would laugh quietly, drawing his own stars alongside Daniel's.

Then came a day that Chester thought would ruin it all.

Their literature class had a substitute who had an attendance list. An attendance list without their preferred names on it. Chester hadn't really realized this, as most of the kids in the class went by their legal names, but after Lilly's name being called and her raising her hand, his heart dropped.

"Cecily Hanes?"

His heart didn't drop it plummeted through the bottom of his ribs and landed in his stomach where his heart shriveled and screamed in the acid.

Taking a deep, shaky breath, Chester lifted his hand. "Here," he cleared his throat. "I, uh, go by Chester though."

Life's hard when you're a horny teenage boy and you're transgender.

The sub just goes on through attendance, calling Daniel's name and moving on.

Daniel stares at Chester for a moment before his lips (Oh god his lips don't think about that) moved into a wolfish grin.

"Cecily?"

"Yep. That's my legal name."

"Okay Cecily,"

"Chester."

"Cecily,"

"Chester," he tries to keep a smile to his face, however the blush from the incident only a minute before lingers.

"I dunno, I like Chester. I think it fits her more," Lilly cuts in, the feminine pronouns cutting into Chester's heart.

He wasn't really out at school. His teachers knew and he had hoped they would follow his request to use male pronouns and the other kids would catch on, but no real luck. All the teachers either forgot or just didn't use pronouns at all and called him 'kiddo' (which he was okay with, better than being called a girl).

"Really?" Comes Daniel's reply. The two go on a bit more, Daniel shrugging after a bit and turning back to him. "Okay, Chester," he says with a grin.

The months he had in that semester class were torturous. Chester hated having crushes, them leaving him feeling awkward and too nervous to even try and establish an actual relationship. But Daniel was actually flirting (well, what he hoped was flirting) with him.

Then came a second unforgettable day in the class.

That day Chester had brought a putty eraser, mostly to play with in his long and skittish fingers rather than actually erase much.

He moved it between his thumb and fingers, moving it to his left hand when needing to write, and then Daniel noticed.

"Hey," he said. "What's that?"

"Oh, it's just an eraser," Chester scribbled lightly on his paper and then rubbed it out with the blob of grey putty. "See?"

"Oh cool, can I see it?"

"Yeah, totally," he pulled half of it apart and handed it to Daniel, noticing way too much how his fingers felt as he passed the eraser to him.

After a few minutes passed, Daniel handed the eraser back to Chester, seemingly pleased with himself.

Chester's eyes widened and he smiled, "Oh," The grey blobby eraser had been make shifted into a small rose. He gently put it on top of one of his eraser-less mechanical pencils, the green one, so the little flower had a stem.

That day Daniel had also drawn a rose on a small piece of paper, Chester drawing one as well, but a bit more artistically.

"Show off," Daniel had laughed.

Months later, that having been November and now it was close to summer and graduation, Chester still had the pencil and paper, the pencil in a jar with other pens and markers (the flower squished from his bookbag) and the paper tucked away in his phone case.

It was a bit embarrassing but in all his 18 years of life no one had ever been that romantic to Chester.

Unfortunately, Lady Luck (or, well, more like the randomized class schedule system) wasn't on Chester's side. The two both had a horribly boring and mundane essay/typing class the next semester but they were split into different class periods.

He still saw and passed Daniel in the hallways, but it was hard to try and talk during that 3 second pass. It was also super hard to not stare at the other boy, despite feeling the other boy's eyes on him as well.

Chester couldn't help but have their whole history flash in his mind every time he thought about Daniel, and, well, that was a lot.


	2. That Itch You Can't Control

**Summary for the Chapter:**

> Imaginary Daniel is Cool (' v' )b

**Notes for the Chapter:**

> Note: HA sorry this one is super nsfw uh sorry>??? but also not but also yes??? whoops anyways heres 1.5k of a teen boy str8 up jerkin it

Chester stares at himself in the mirror, face now wet but still bright pink and hair in its usual bedhead style. He sighs again, heart fluttering (stop it, god please, why), and feeling like a total wreck. He glances at his phone, he still has a good hour or so until anyone should get home. "God," he mumbles, "I'm pathetic," yet decides to continue what he decided to do, this time maybe a level higher.

Once again he lifts the large sweater, holding it up with his teeth, and staring at himself in the mirror and pumping up his confidence.

He was kind of awkward looking, being chubby and having more hips and breasts than the average guy, but with the right lighting and angling he could be hot.

He lifts his fingers up and gently moves his septum ring back into an even place, disheveled could be sexy, just not quite yet.

After adjusting the small silver ring, his hands slowly go back down to his torso, gently grabbing his breasts. He didn't like them that much, they ruined his ability to pass they were too large to conceal even in a binder, but they were some damn good breasts. Large and full, soft and sensitive, Chester often wished he could just donate his breasts to someone who needed them more than he did. He'd like to keep his nipples however, they were sensitive and it might be fun to have pierced nipples once his chest was flat. He ignores all the deeper shit, and just tries to appreciate the aesthetics of his body.

Full, soft breasts hanging over his pale chest. Strong ribs lead to the soft belly which gently curved, a few stretch marks around, but still beautiful enough. His hands followed it down to his hips, boney like the rest of him (he was so boney, of course it'd be nice to be skinny but he'd probably also injure many people with his odd bones) but still covered in a soft layer of skin and a small amount of fat. He doesn't let his hands travel down his boxers (also oversized, it was difficult to know what size you are in men's clothing especially for underwear and especially when the size on the shelf doesn't match the actual size on the package) yet, but he's familiar with his own soft thighs and legs and everything in between.

It's his body in its purest form.

Chester lets the sweatshirt drop from his mouth, momentarily biting his lips before unlocking the bathroom door and heading back to his room.

Back inside his own safe haven, he locks his own door and sheds his underwear. Grabbing his laptop and putting on his specific playlist, he gets into bed.

Living in a house with prying eyes and thin walls makes one not so eager to be loud or even out in the open, so Chester does as always and covers himself with at least a sheet before letting himself get to work.

He lays back, messy golden hair resting upon a well-worn pillow and now chilly hands sneaking under his covers. He scrunches his nose up, knowing that it's so creepy and possibly wrong and bad, but begins to imagine his hands are Daniel's.

This isn't the first time he done it, it probably won't be the last, but it always makes him feel a little guilty using someone else in his fantasies. But then he also imagines someone else masturbating to the thought of him and it couldn't be more of a turn on.

Chester breathes slowly and lightly as his-no, Daniel's- hands run over his chest. Gently caressing the soft breasts there and slowly playing with his nipples, he can feel his cock tingling already. A soft breath escapes him as he imagines kisses running up his chest to his neck to his lips and focuses on the hands softly making their way down his body. They tickle at the small dip from his belly to his pelvis, causing a small shudder to run up his spine.

He can feel himself getting wet, getting excited and little sparks begin, but no, not yet. Daniel's the teasing type there's no way he would let Chester get off this quickly. Hands find their way to the inside of his thighs, playing with the smooth skin there, running over that one mole he's had forever. He breaths a little harder, imagining Daniel taking notice and kissing the small mark, so close to his cock he can feel Daniel's stubble brushing against his skin, but still, not yet. Chester's cock gets more excited as the hands continue to play, moving up again to his breasts, imagining the other boy placing more kisses and marks along the inside of his thighs. His cock twitches and he really wants to pay attention to it, he really does, but he waits. The longer it takes the better.

The hands move along his hips again, gently and hardly brushing his cock, but still ignoring the poor thing.

Chester can already feel his face blushing and bites his lip, imagining It was someone else. Oh god, how nice would that be? Making out has always sounded really great, god, he wants to make out with someone-with Daniel.

His legs move under the sheets, restless and trying to get any kind of friction where it needs to go, but they do this to no avail.

The hands run along his arms, lanky and muscular from marching band, freckles covering them from shoulder to knuckle from the sun.

He breathes heavier, his breath sometimes shuddering in his throat before he can get it out. Even in the empty house he doesn't let himself make much noise, he never has. Only small squeaks and even smaller moans make themselves heard.

Everything seems to be going smooth and simple, but Imaginary Daniel has some ideas of his own.

Chester's heart picks up and he bites his lip more as he imagines the bright-eyed, super flirty, super nice and hot boy grinding his erection along Chester's own.

"Shit, shit, shit," repeatedly runs through his mind.

He finally gives in and lets his right hand explore more in depth. Despite being his more dominant hand (mainly, he can write with it, being ambidextrous means both hands are pretty good at what they do when you practice a bit) being more clumsy in this area, his left hand usually taking lead, it allows him to give Imaginary Daniel a little more realism, pretending that it's his own dominant left hand.

Chester releases a breathy sigh when the hand finally gives his cock some attention. His clit now erect and the rest of himself wet.

His diaphragm begins to move more as his breaths grow deeper and he can practically hear Imaginary Daniel whispering into his ear.

"God," the phantom sighs as he gently massages the real boy. "You know how handsome you are when you're like this? How hot you are? God, I adore you,"

Chester's heart and eyelids flutter to this, the hand at the same time of the unspoken words moving deeper into his cock. A large sigh forces itself out of his chest, his breathing becoming more erratic and full.

Two fingers find his way into his mouth while two others begin to fuck the boy, the palm they belong to keeping a steady pressure on his clit.

"God, look at you," comes the deep voice of Daniel, the imaginary boy leaving imaginary soft kisses and gentle bites along Chester's neck and collarbone. "Will you come for me soon?"

Chester gives a small whine, his whole body quivering and sweating, it feels like he's made from pop rocks and has spilled pop all over himself, his heart beating and fluttering from just the idea of it all, the rest from his own touches.

He forgets what pushes him over the edge, soft spoken words from Imaginary Daniel? Or just pure desperateness? Whatever it is, he comes hard, his knees crossing and his body shaking, biting his fingers as the endorphins rush through him.

It takes him a minute or so to rebuild himself, to recollect his pieces that go missing for a bit after going so high.

Still breathing heavily, he covers his face with his hands and smiles a bit. "Jesus, god, fuck, god, shit," his mind races a bit before forming coherent thoughts. His face flushes even more than what it was once he registers what he just did.

Slowly, he repeats his ritual to clear his room of anything he deems sex-ish and goes to take a shower.

His breathing returns to normal but his heart still races, god, he just can't get the other boy out of his head. The shower is relatively quick, leaving him enough time to change into a t-shirt and some sweatpants and to go downstairs for a granola bar and some water.

Chester Hanes tries not to think about it, let alone be embarrassed about it (it's totally normal, teenagers do that stuff!) but he still manages to write in his journal for that day, "Big virgin, even bigger dweeb."

God.

Life's hard.


End file.
